GB1173290A - Piperidine Nitroxides and process for preparing the same - Google Patents
Piperidine Nitroxides and process for preparing the sameInfo
- Publication number
- GB1173290A GB1173290A GB52848/66A GB5284866A GB1173290A GB 1173290 A GB1173290 A GB 1173290A GB 52848/66 A GB52848/66 A GB 52848/66A GB 5284866 A GB5284866 A GB 5284866A GB 1173290 A GB1173290 A GB 1173290A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- arylene
- formula
- amino
- reaction
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- -1 Piperidine Nitroxides Chemical class 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002841 Lewis acid Substances 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000000732 arylene group Chemical group 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000002993 cycloalkylene group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 150000007517 lewis acids Chemical class 0.000 abstract 1
- 150000004967 organic peroxy acids Chemical class 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 150000002978 peroxides Chemical class 0.000 abstract 1
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical class O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/20—Spiro-condensed ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
- C07D211/94—Oxygen atom, e.g. piperidine N-oxide
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
1,173,290. Piperidine nitroxide derivatives. SANKYO CO. Ltd. 25 Nov., 1966 [24 Aug., 1966], No. 52848/66. Heading C2C. [Also in Division C3] Compounds of the formula where R 1 and R 2 , which may be the same or different, represent an alkyl group or, together with the carbon atom to which they are attached form a 5- to 7-membered cycloalkyl ring, R 3 represents an alkylene group, a cycloalkylene group with a 5- to 7-membered ring, an arylene group which may be substituted by alkyl, alkoxy or amino in the aryl moiety, or an arylene amino or arylene-diamino group and X is hydrogen or the group may be obtained by reacting a compound of the formula with a compound of the formula H 2 N-R 3 -Y where Y represents hydrogen or an amino group. The reaction may be effected in a solvent at room temperature or by refluxing the reactants in a water-immiscible organic solvent and preferably removing water from the reaction as it is formed, and a conventional condensation catalyst may be present. The starting materials, some of which are stated to be novel compounds, may be obtained by reacting diacetone alcohol with a suitable ketone and ammonia in the presence of a Lewis acid to produce the corresponding piperidone derivative followed by treatment of the latter with a suitable peroxide, e.g. H202, or an organic peracid.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5597266 | 1966-08-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1173290A true GB1173290A (en) | 1969-12-03 |
Family
ID=13013973
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB52848/66A Expired GB1173290A (en) | 1966-08-24 | 1966-11-25 | Piperidine Nitroxides and process for preparing the same |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3503982A (en) |
| DE (1) | DE1620429A1 (en) |
| FR (1) | FR1503149A (en) |
| GB (1) | GB1173290A (en) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3684765A (en) * | 1970-01-08 | 1972-08-15 | Sankyo Co | Stabilization of synthetic polymers |
| GB1395159A (en) * | 1971-11-30 | 1975-05-21 | Ciba Geigy Ag | Tetra-hydropyridine derivatives |
| JPS4964634A (en) * | 1972-10-25 | 1974-06-22 | ||
| DE2612314A1 (en) * | 1976-03-23 | 1977-09-29 | Bayer Ag | PIPERIDE DERIVATIVES AS LIGHT PROTECTION AGENTS |
| DE3021955A1 (en) * | 1980-06-12 | 1981-12-24 | Chemische Werke Hüls AG, 4370 Marl | METHOD FOR PRODUCING PRIMARY MONO- AND DIAMINES FROM OXO COMPOUNDS |
| EP0097616B1 (en) * | 1982-06-17 | 1986-08-20 | Ciba-Geigy Ag | Polyalkylpiperidine esters of sulfonic acids |
| SG82601A1 (en) * | 1998-03-09 | 2001-08-21 | Ciba Sc Holding Ag | 1-alkoxy-polyalkyl-piperidine derivatives and their use as polymerization regulators |
| US7199245B2 (en) * | 2001-06-13 | 2007-04-03 | Ciba Specialty Chemicals Corp. | 4-imino-n-alkoxy or oxy-polyalkyl-piperidine compounds and their use as polymerization regulators |
| CN115108969B (en) * | 2022-05-20 | 2024-03-29 | 华南理工大学 | Efficient migration-resistant antioxidant and preparation method and application thereof |
-
1966
- 1966-11-25 GB GB52848/66A patent/GB1173290A/en not_active Expired
- 1966-11-25 US US596755A patent/US3503982A/en not_active Expired - Lifetime
- 1966-11-26 DE DE19661620429 patent/DE1620429A1/en active Pending
- 1966-12-02 FR FR85906A patent/FR1503149A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR1503149A (en) | 1967-11-24 |
| US3503982A (en) | 1970-03-31 |
| DE1620429A1 (en) | 1970-04-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |